CN105399713A - Novel benzene peptide derivative and preparation method and application thereof - Google Patents

Novel benzene peptide derivative and preparation method and application thereof Download PDF

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CN105399713A
CN105399713A CN201510973784.0A CN201510973784A CN105399713A CN 105399713 A CN105399713 A CN 105399713A CN 201510973784 A CN201510973784 A CN 201510973784A CN 105399713 A CN105399713 A CN 105399713A
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preparation
benzene peptide
peptide derivant
silica gel
column chromatography
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CN105399713B (en
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秦波
潘乐
李秀壮
金辉
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Lanzhou Institute of Chemical Physics LICP of CAS
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    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/90—Benzo [c] furans; Hydrogenated benzo [c] furans with an oxygen atom in position 1 and a nitrogen atom in position 3, or vice versa
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Abstract

The present invention discloses a novel benzene peptide derivative, and the benzene peptide derivative has a general formula shown as formula I, wherein R is shown in the specification. The present invention also discloses a preparation method and application of the derivative. The derivative has the characteristics of being excellent in activity and environment-friendly, and provides a new choice for prevention and treatment of plant pathogenic fungi. The preparation method is easy to operate, raw material price is low, yield is high, and the preparation method has a good cost advantage.

Description

Novel benzene peptide derivant and its preparation method and application
Technical field
The present invention relates to series of new benzene peptide derivant and its preparation method and application.
Background technology
Plant pathogenic fungi is one of main agricultural disease, and the financial loss caused in the world every year exceedes 2,000,000,000 U.S. dollars.Chemical pesticide is due to instant effect, and has a broad antifungal spectrum is the important means of pathogenic bacteria control all the time.But along with the long-time application of traditional agricultural chemicals, the problems such as environmental toxicity, food safety and germ resistance become its significant challenge faced.Thus, the research and development of novel agrochemical substitute and new texture become instant task.
Benzene peptide class formation is the essential building blocks of a lot of natural product and chemicals, is also the key structure composition of some important enzyme inhibitor.In agriculture production, benzene peptide derivative-tetrachlorobenzene peptide is successfully developed as plant antimicrobial, for the control of bacterial blight of rice and rice blast.But, faint to the effect of other pathogenic fungies, and as organochlorine pesticide, this product threatens to environment and food safety.Thus, based on benzene peptide class formation, its structure is modified and is transformed the effective way probably becoming and find new substitute.Based on this, the present invention has designed and synthesized serial benzene peptide derivative, and is studied its anti-fungal activity of plant pathogenic.Result shows, the serial benzene peptide derivative related in the present invention has the different excellent activity of degree.
Summary of the invention
The invention provides a series of benzene peptide derivant and its preparation method and application, this compounds has the different excellent activity of degree to various plants fungi.
Novel benzene peptide derivant, is characterized in that the general formula of this benzene peptide derivant is such as formula I:
Wherein, R is:
。
The preparation method of benzene peptide derivant described above, is characterized in that concrete steps are as follows:
By 2-carboxyl benzaldehyde and primary amine stirring reaction 1 ~ 3 hour under room temperature condition in methyl alcohol, filter, with the washing with alcohol solid of 95%, obtain crude product, then will concentrate after crude product purification by silica gel column chromatography and obtain benzene peptide derivant.
Described primary amine is 5-aminoisoquinoline, 2-amino-5-thiazol formic-acid ester, meta-aminophenol, 5-aminophthalic acid, 5-quinolylamine, 8-quinolylamine, 7-aminocoumarin or the chloro-5-aminopyridine of 2-.
The mol ratio of described 2-carboxyl benzaldehyde and primary amine is 1:1 ~ 1.2:1.
Chloroform and the methyl alcohol of the eluent of described silica gel column chromatography to be volume ratio be 40:1 ~ 10:1.
Described novel benzene peptide derivative is as the application of plant epiphyte resisting agent.
Compared with existing anti-mycotic agent, the design of novel benzene peptide derivant of the present invention, synthesis and as the application of anti-mycotic agent with 2-carboxyl benzaldehyde for source, have good activity, eco-friendly feature, the control for plant pathogenic fungi provides new selection.The synthetic method easy handling that the present invention relates to, low in raw material price, productive rate is higher, has good cost advantage.
Embodiment
Embodiment 1:3-[(isoquinoline 99.9-5-base) is amino]-2-cumarone-1 (3H)-one (I a)
1H-NMR(CHCl 3-d,400MHz)δ:5.22(d,1H,J=9.8Hz),6.94(d,1H,J=9.8Hz),7.56-7.59(m,1H),7.56-7.59(m,1H),7.61-7.67(m,4H),7.69-7.73(m,1H),7.76-7.85(m,1H),7.99(d,1H,J=7.6Hz),8.50(d,1H,J=6.0Hz),9.25(s,1H); 13C-NMR(CHCl 3-d,100MHz)δ:87.26,113.56,114.53,121.09,123.46,125.91,127.45,127.88,127.93,129.18,131.15,134.70,138.44,142.52,145.23,152.89,168.98.
At room temperature, 2-carboxyl benzaldehyde (1.1mol) and 5-aminoisoquinoline (1mol) are in methanol solvent system, and stirring reaction filters for 1 hour, and the solid washing with alcohol of 95%, obtains crude product.Concentrate after silica gel column chromatography (eluent: chloroform/methanol (40/1)) purifying and obtain white solid, productive rate 80%.
Embodiment 2:3-[(5-thiazol formic-acid ester-2-base) is amino]-2-cumarone-1 (3H)-one (I b)
1H-NMR(CHCl 3-d,400MHz)δ:1.27(t,3H,J=6.8Hz),4.24(dd,2H,J=14Hz,6.8Hz),7.25(d,1H,J=9.2Hz),6.12(s,1H),7.73(t,1H,J=7.2Hz),7.78(d,1H,J=7.6Hz),7.86(t,1H,J=7.6Hz),7.91(d,1H,J=6.0Hz); 13C-NMR(DMSO-d 6,400MHz)δ:14.71,61.23,85.38,118.67,124.55,125.35,127.26,131.36,135.23,145.41,147.27,161.51,169.01,171.22.
At room temperature, 2-carboxyl benzaldehyde (1.1mol) and 2-amino-5-thiazol formic-acid ester (1mol) are in methanol solvent system, and stirring reaction filters for 1 hour, and the solid washing with alcohol of 95%, obtains crude product.Concentrate after silica gel column chromatography (eluent: chloroform/methanol (40/1)) purifying and obtain white solid, productive rate 82%.
Embodiment 3:3-[(phenol-3-base) is amino]-2-cumarone-1 (3H)-one (I c)
1H-NMR(DMSO-d 6,400MHz)δ:4.07-4.12(m,1H),5.20(s,2H),5.96(dd,1H,J=2.0,8.4Hz),6.09(d,1H,J=2.0Hz),6.48(d,1H,J=8.4H),6.65(s,1H),7.39(d,1H,J=7.6Hz),7.58(d,1H,J=7.6Hz),7.71(d,1H,J=7.6H),7.84(d,1H,J=7.6H),9.36(s,1H); 13C-NMR(DMSO-d 6,100MHz)δ:84.68,105.82,110.62,114.70,128.22,129.72,131.24,134.02,134.21,139.35,155.88,156.19,162.09.
At room temperature, 2-carboxyl benzaldehyde (1.1mol) and meta-aminophenol (1mol) are in methanol solvent system, and stirring reaction filters for 1 hour, and the solid washing with alcohol of 95%, obtains crude product.Concentrate after silica gel column chromatography (eluent: chloroform/methanol (40/1)) purifying and obtain white solid, productive rate 80%.
Embodiment 4:3-[(3,4-dicarboxyl benzene-3-base) is amino]-2-cumarone-1 (3H)-one (I d)
1H-NMR(CHCl 3-d,400MHz)δ:7.04(d,2H,J=7.2Hz),7.24(d,1H,J=10.0Hz),7.70-7.78(m,3H),7.86(d,1H,J=7.2Hz),7.90-7.94(m,2H); 13C-NMR(CHCl 3-d,400MHz)δ:86.86,112.99,114.76,124.61,125.29,127.58,131.18,131.65,137.91,145.90,148.79,167.67,169.33,170.37.
At room temperature, 2-carboxyl benzaldehyde (1.1mol) and 5-aminophthalic acid (1mol) are in methanol solvent system, under Tetrabutyl amonium bromide (0.03mol) catalysis, stirring reaction is after 1 hour, solvent removed in vacuo, the solid washing with alcohol of 95%, obtains crude product.Concentrate after silica gel column chromatography (eluent: chloroform/methanol (40/1)) purifying and obtain white solid, productive rate 86%.
Embodiment 5:3-[(quinoline-5-base) is amino]-2-cumarone-1 (3H)-one (I e)
1H-NMR(DMSO-d 6,400MHz)δ:7.29(d,1H,J=10.4Hz),7.43(dd,1H,J=2.4,5.6Hz),7.61-7.63(m,2H),7.73-7.82(m,3H),7.86-7.94(m,2H),8.05(d,J=6.0Hz),8.32(s,1H),8.45(d,J=6.0Hz); 13C-NMR(DMSO-d 6,100MHz)δ:88.29,112.22,115.62,119.43,124.84,125.11,127.02,127.81,128.39,129.41,130.98,134.92,140.59,142.50,146.41,152.83,169.60.
At room temperature, 2-carboxyl benzaldehyde (1.1mol) and 5-quinolylamine (1mol) are in methanol solvent system, and stirring reaction filtered after 1 hour, and the solid washing with alcohol of 95%, obtains crude product.Concentrate after silica gel column chromatography (eluent: chloroform/methanol (40/1)) purifying and obtain white solid, productive rate 90%.
Embodiment 6:3-[(quinoline-8-yl) is amino]-2-cumarone-1 (3H)-one (I f)
1H-NMR(CHCl 3-d,400MHz)δ:7.05(d,1H,J=9.6Hz),7.34(t,2H,J=7.2Hz),7.42(dd,1H,J=8.0Hz,4.0Hz),7.51(t,1H,J=8.0Hz),7.65-7.69(m,1H),7.77(dd,1H,J=7.2Hz,4.0Hz),7.98(d,1H,J=7.6Hz),8.15(d,1H,J=8.0Hz),8.71(dd,1H,J=4.0Hz,1.2Hz); 13C-NMR(CHCl 3-d,100MHz)δ:86.37,118.39,121.82,123.59,125.84,127.55,128.19,128.75,130.89,134.55,140.72,145.59,169.43.
At room temperature, 2-carboxyl benzaldehyde (1.1mol) and 8-quinolylamine (1mol) are in methanol solvent system, and stirring reaction filtered after 1 hour, and the solid washing with alcohol of 95%, obtains crude product.Concentrate after silica gel column chromatography (eluent: chloroform/methanol (40/1)) purifying and obtain white solid, productive rate 85%.
Embodiment 7:3-[(chromen-2-one-7-base) is amino]-2-cumarone-1 (3H)-one (I g)
1H-NMR(CHCl 3-d,400MHz)δ:2.41(s,3H),5.12-5.13(m,1H),6.13(s,1H),6.37(s,1H),6.86-6.90(m,3H),7.04-7.06(m,1H),7.51-7.56(m,2H),7.62-7.69(m,4H),7.74-7.79(m,1H),7.90(d,1H,J=7.6Hz),7.97(d,1H,J=7.6Hz); 13C-NMR(CHCl 3-d,100MHz)δ:18.53,86.78,100.55,110.51,111.92,112.38,124.59,125.32,126.89,127.56,131.22,135.08,145.82,149.69,154.00,155.34,160.79,169.33.
At room temperature, 2-carboxyl benzaldehyde (1.1mol) and 7-aminocoumarin (1mol) are in methanol solvent system, and stirring reaction filtered after 1 hour, and the solid washing with alcohol of 95%, obtains crude product.Concentrate after silica gel column chromatography (eluent: chloroform/methanol (40/1)) purifying and obtain white solid, productive rate 80%.
Embodiment 8:3-[(the chloro-pyridine of 2--6-base) is amino]-2-cumarone-1 (3H)-one (I h)
1H-NMR(CHCl 3-d,400MHz)δ:5.31-5.33(m,1H),6.76-6.78(m,2H),3.88(s,3H),6.91(s,1H),7.64-7.72(m,2H),7.78-7.82(m,1H),7.98(d,1H,J=7.2Hz),8.16(d,1H,J=3.6Hz); 13C-NMR(DMSO-d 6,100MHz)δ:85.35,108.22,109.58,124.61,125.41,127.27,131.37,135.24,145.50,150.32,151.68,154.71,169.10.
At room temperature, 2-carboxyl benzaldehyde (1.1mol) and the chloro-5-aminopyridine (1mol) of 2-are in methanol solvent system, and stirring reaction filtered after 1 hour, and the solid washing with alcohol of 95%, obtains crude product.Concentrate after silica gel column chromatography (eluent: chloroform/methanol (40/1)) purifying and obtain white solid, productive rate 80%.
With 4 kind of plant pathogenic fungies for model, the anti-mycotic activity of synthesized benzene peptide derivant is screened.
Test plant pathogenic fungi: alternaric bacteria ( alternariaalternate, A.alternate) ,alternaria solani ( alternariasolani, A.solani) ,the pathogen of Botrytis cinerea ( botrytiscinerea, B.cinerea) and cotton-wilt fusarium ( fusariumoxysporum, F.oxysporum).This test adopts the malicious flat band method of band to carry out screening active ingredients.Before using, at 25 DEG C, carry out rejuvenation to for examination fungi.
Test liquid prepares: test sample is dissolved in dimethyl sulfoxide (DMSO) the solution forming 200mg/L, before use with distilled water diluting to desired concn, adopt coubling dilution to obtain the test liquid of series concentration gradient, ensure that in final test liquid, dimethyl sulfoxide concentration is no more than 1%.
Test method: in gnotobasis, the sterilized PDA substratum of test liquid is diluted to desired concn, and to be poured into diameter be in the culture dish of 6cm, after culture medium solidifying, with inoculating needle, the bacterium cake (0.5cm) prepared is placed in dull and stereotyped central authorities, culture dish sealing is placed on 25 DEG C of dark culturing.After 5 days, observe fungal growth situation, and measure bacterial plaque size, add up and calculate its proofread inhibit rate.Often process repetition 3 times, test repetition 2 times.Inhibiting rate calculation formula: inhibiting rate (%)=(C-T) × 100/C (C: negative control group bacterial plaque diameter; T: treatment group bacterial plaque diameter).The activity of above-mentioned 8 kinds of novel benzene peptide derivative anti-plant pathogenic fungis sees the following form.
。

Claims (6)

1. novel benzene peptide derivant, is characterized in that the general formula of this benzene peptide derivant is such as formula I:
Wherein, R is:
。
2. the preparation method of benzene peptide derivant as claimed in claim 1, is characterized in that concrete steps are as follows:
By 2-carboxyl benzaldehyde and primary amine stirring reaction 1 ~ 3 hour under room temperature condition in methyl alcohol, filter, with the washing with alcohol solid of 95%, obtain crude product, then will concentrate after crude product purification by silica gel column chromatography and obtain benzene peptide derivant.
3. preparation method as claimed in claim 2, is characterized in that described primary amine is 5-aminoisoquinoline, 2-amino-5-thiazol formic-acid ester, meta-aminophenol, 5-aminophthalic acid, 5-quinolylamine, 8-quinolylamine, 7-aminocoumarin or the chloro-5-aminopyridine of 2-.
4. preparation method as claimed in claim 2, is characterized in that the mol ratio of described 2-carboxyl benzaldehyde and primary amine is 1:1 ~ 1.2:1.
5. preparation method as claimed in claim 2, is characterized in that the eluent of described silica gel column chromatography to be volume ratio is chloroform and the methyl alcohol of 40:1 ~ 10:1.
6. as claimed in claim 1 novel benzene peptide derivative as the application of plant epiphyte resisting agent.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113200989A (en) * 2021-05-18 2021-08-03 云南民族大学 Preparation method and application of chromone alkaloid compound
CN113979976A (en) * 2021-11-09 2022-01-28 上饶师范学院 Method for synthesizing nitrogen-containing phthalide compound at normal temperature

Citations (1)

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Publication number Priority date Publication date Assignee Title
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